Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
  • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
  • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/002—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor using materials containing microcapsules; Preparing or processing such materials, e.g. by pressure; Devices or apparatus specially designed therefor
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C1/00—Photosensitive materials
  • G03C1/002—Photosensitive materials containing microcapsules
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
  • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
  • Y10S430/1055—Radiation sensitive composition or product or process of making
  • Y10S430/114—Initiator containing
  • Y10S430/122—Sulfur compound containing
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
  • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
  • Y10S430/1055—Radiation sensitive composition or product or process of making
  • Y10S430/127—Spectral sensitizer containing

Definitions

• the present invention relates to a photosensitive recording material using microcapsules, and in particular to a photosensitive recording material using microcapsules that contain core materials in a specific combination.
• the microcapsules are commonly applied over the entire surface of the recording medium, the surface of the photosensitive recording material is exposed to form a latent image based on the image that is to be recorded, and the recording medium on which the latent image has been formed is pressurized to visualize and record the image.
• the microcapsules harden in the portions that is exposed, but do not harden in the unexposed portions, and since the capsules themselves are not destroyed by pressure in the portions where the microcapsules have hardened, they do not colorize in the portions where they have hardened when the recording medium on which the latent image has been formed is pressurized by a pressurization device, while the microcapsules are destroyed according to the wavelength of the exposure light in the portions where the capsules have not hardened, resulting in the development of color by a coloring reaction.
• microcapsules sometimes do not harden sufficiently when exposed, and even those which are known to be highly sensitive do not harden sufficiently.
• An object of the present invention is to remedy the aforementioned drawbacks by providing a photosensitive recording material in which microcapsules can be sufficiently hardened with low energy, and which is capable of forming clear images with good tone and no smearing.
• the present invention provides a photosensitive recording material comprising a support and microcapsules provided thereon, wherein the microcapsules comprises a photopolymerizable unsaturated group-containing compound and a phosphine compound represented by the following general formula: where R 1 , R 2 and R 3 indicate a hydrogen atom, a C 1 to C 20 alkyl, aryl or aralkyl group, -OR 4 , or -SR 4 where R 4 indicates a hydrogen atom or a C 1 to C 20 alkyl, aryl or aralkyl group, and these may be substituted by a halogen atom or a C 1 to C 20 alkoxy, alkoxycarbonyl, acyloxy, alkanoyl, cyano, hydroxy or amino group.
• the microcapsules comprise the photopolymerizable unsaturated group-containing compound and the phosphine compound represented by the aforementioned general formula
• the microcapsules are allowed to be sufficiently hardened with low energy, and clear images are also allowed to be formed with good tone and no smearing.
• the photopolymerizable unsaturated group-containing compound is preferably a polymerizable compound having at least one ethylenic unsaturated double bond. This allows the microcapsules to be sufficiently cured rapidly, and clear images with good tone and no smearing to be formed.
• the phosphine compound is contained in an amount of from 0.01 to 20 wt%. This allows the microcapsules to be sufficiently cured rapidly with low energy, and clear images with good tone and no smearing to be formed.
• the photosensitive recording material of the present invention comprises a support and microcapsules provided thereon, where the microcapsules comprises a photopolymerizable unsaturated group-containing compound and a phosphine compound.
• Examples of the aforementioned photopolymerizable unsaturated group-containing compound include compounds having ethylenic unsaturated groups and compounds having epoxy groups.
• the compounds having ethylenic unsaturated groups with a relatively fast velocity of photopolymerization are especially preferred.
• Examples of the compounds having ethylenic unsaturated groups include acrylic acid and salts thereof, acrylic acid esters, acrylamide, methacrylic acid and salts thereof, methacrylic acid esters, methacrylamides, maleic anhydride, maleic anhydride esters, itaconic acid esters, styrenes, vinyl ethers, vinyl esters, N -vinyl heterocycles, allyl ethers, allyl esters, and derivatives thereof.
• acrylic acid esters or methacrylic acid esters with a relatively rapid degree of photopolymerization are especially preferred.
• acrylic acid esters include butyl acrylate, cyclohexyl acrylate, ethylhexyl acrylate, benzyl acrylate, furfuryl acrylate, ethoxyethyl acrylate, tricyclodecanyloxy acrylate, nonylphenyloxyethyl arylate, hexanediol acrylate, 1,3-dioxolan acrylate, hexanediol diacrylate, butanediol diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, tricyclodecane dimethylol diacrylate, tripropylene glycol diacrylate, bisphenol A diacrylate, pentaerythritol triacrylate, dipentaerythritol hexacrylate, dipentaerythritol caprolactone-adduct hexacrylate, trimethylol propane triacrylate, tri
• methacrylic acid esters examples include butyl methacrylate, cyclohexyl methacrylate, ethylhexyl methacrylate, benzyl methacrylate, furfuryl methacrylate, ethoxyethyl methacrylate, tricyclodecanyloxy methacrylate, nonylphenyloxyethyl methacrylate, hexanediol methacrylate, 1,3-dioxolan methacrylate, hexanediol dimethacrylate, butanediol dimethacrylate, neopentyl glycol dimethacrylate, polyethylene glycol dimethacrylate, tricyclodecane dimethylol dimethacrylate, tripropylene glycol dimethacrylate, bisphenol A dimethacrylate, pentaerythritol trimethacrylate, dipentaerythritol hexamethacrylate,
• These polymerizable compounds may be used individually or in combinations of two or more.
• the aforementioned acrylic acid esters or methacrylic acid esters preferably contains at least one of pentaerythritol triacrylate, dipentaerythritol hexacrylate, dipentaerythritol caprolactone-adduct hexacrylate, trimethylol propane triacrylate, and trimethylol propane propylene oxide-adduct triacrylate, which have three or more aryloyl groups, which are unsaturated groups, per molecule.
• the photopolymerizable unsaturated group-containing compound also contains the phosphine compound represented by the following general formula: where R 1 , R 2 and R 3 indicate a hydrogen atom, a C 1 to C 20 alkyl, aryl or aralkyl group, -OR 4 , or -SR 4 where R 4 indicates a hydrogen atom or a C 1 to C 20 alkyl, aryl or aralkyl group, and these may be substituted by a halogen atom or a C 1 to C 20 alkoxy, alkoxycarbonyl, acyloxy, alkanoyl, cyano, hydroxy or amino group.
• R 1 , R 2 and R 3 indicate a hydrogen atom, a C 1 to C 20 alkyl, aryl or aralkyl group, -OR 4 , or -SR 4 where R 4 indicates a hydrogen atom or a C 1 to C 20 alkyl, aryl or aralkyl group, and these may be substitute
• phosphine compounds include phosphate esters, phosphite esters, thiophosphate esters, thiophosphite esters, and derivatives thereof. Of these, thiophosphite derivatives with high sensitivity to light and good hardening properties are especially preferred.
• the phosphine compound is added in an amount of 0.01 to 20 wt%, and preferably 0.5 to 10 wt%, with respect to the photopolymerizable unsaturated group-containing compound. Less than 0.01 wt% results in poor improvement, while more than 20 wt% results in extremely poor storage stability.
• the photosensitive recording material of the present invention may contain a photopolymerization initiator, a photosensitizer such as a sensitizing colorant, a stabilizer such as a heat polymerization inhibitor, compatibility improving agent, a pigment or the like in addition to the aforementioned essential components.
• a photopolymerization initiator such as a sensitizing colorant
• a stabilizer such as a heat polymerization inhibitor
• compatibility improving agent such as a pigment or the like in addition to the aforementioned essential components.
• a highly sensitive photosensitive material can be obtained when a photopolymerization initiator or photosensitizer is added.
• aromatic carbonyl compounds aromatic carbonyl compounds, acetophenones, organic peroxides, diphenylhalonium salts, organic halides, 2,4,6-substituted-S-triazines, 2,4,5-triarylimidazole dimers, azo compounds, dye borate complexes, metal arene complexes, titanocene compounds and the like can be used, which initiates or promotes the polymerization reaction of the aforementioned polymerizable material through light energy.
• photopolymerization initiator benzophenone, benzyl, xanthone, thioxanthone, anthraquinone, acetophenone, 2,2-dimethl-2-morpholino-4'-methylthioacetophenone, benzoyl peroxide, 3,3',4,4'-tetrakis(t-butyldioxycarbonyl)benzophenone, diphenyl iodonium bromide, diphenyl iodonium chloride, carbon tetrachloride, carbon tetrabromide, 2,4,6-tristrichloromethyl-S-triazine, ( ⁇ 5 -2,4-cyclopentadien-1-yl)[(1,2,3,4,5,6- ⁇ )-(1-ethylethyl)benzene]iron(1+)hexafluorophosphate(1-), and the like are preferred. These photopolymerization initiator may be used individually or in combinations
• the photopolymerization initiator is used in a ratio of 0.1 to 20 wt%, and preferably 1 to 10 wt%, with respect to the polymerizable material. Less than 1% ordinarily makes it difficult to produce a photopolymerization reaction, while more than 10% does not increase the sensitivity.
• a sensitizing colorant may also be used to improve the photosensitivity, particularly the photosensitivity to wavelength, of the aforementioned photosensitive recording material.
• Xanthene dyes As the sensitizing colorant, Xanthene dyes, coumarin dyes, mellocyanine dyes, thiazine dyes, azine dyes, methine dyes, oxazine dyes, phenylmethane dyes, cyanine dyes, azo dyes, anthraquinone dyes, pyrazoline dyes, stilbene dyes, quinoline dyes, and the like can be used.
• Pigments can be used as a coloring material. Those of suitable hue may be selected from those that are commercially available as well as those listed in Pigments manuals or other such documents (such as New Pigment Manual [Saishin Ganryo Benran], compiled by Nihon Ganryo Gijutsu Kyokai and published in 1977) in the literature, and are dispersed for use.
• Organic solvents having suitable polarity can also be used to adjust the solubility of the composition encapsulated in the microcapsules of the present invention.
• microcapsules can be manufactured using encapsulation methods which are already well known techniques in the field.
• the methods include phase separation methods from aqueous solutions such as those disclosed in U.S. Patents No. 2,800,457 and 2,800,458, interfacial polymerization methods such as that disclosed in Japanese Patent Publications No. 38-19574, 42-446, and 42-771, in-situ methods based on the polymerization of monomers such as those disclosed in Japanese Patent Publication No. 36-9168 and Japanese Patent Application Laid-Open No. 51-9079, and catalytic dispersion cooling method such as that disclosed in Great Britain Patents No. 952,807 and 965,074.
• microcapsule wall-forming material any inorganic or organic materials, as long as microcapsule walls can be made therefrom in the aforementioned capsule manufacturing methods, can be used.
• the microcapsule wall-forming material is preferably to exhibit excellent light-transmissive.
• microcapsule wall-forming material examples include gelatin, gum arabic, starch, sodium alginate, polyvinyl alcohol, polyethylene, polyamides, polyester, polyurethane, polyurea, polystyrene, nitrocellulose, ethylcellulose, methylcellulose, melamine-formaldehyde resins, urea-formaldehyde resins, and the like, as well as copolymers thereof.
• Melamine-formaldehyde resins or urea-formaldehyde resins which can be produced in a relatively simple manufacturing method, are preferred when the in-situ method is used, in which the wall starting material is supplied in water.
• the composition serving as the encapsulation material must be dispersed or emulsified in an aqueous medium.
• the aqueous medium should contain a nonionic or anionic water-soluble polymer.
• nonionic water-soluble polymers examples include polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, polymethylvinyl ether, hydroxymethylcellulose, and hydroxyethylcellulose.
• anionic water-soluble polymers examples include polystyrenesulfinic acid, polystyrenesulfonates, styrenesulfonic acid copolymers, polyvinyl sulfuric acid ester salts, polyvinylsulfonates, maleic anhydride-styrene copolymers, and maleic anhydride-isobutylene copolymers.
• Examples of materials used as the recording medium for the photosensitive recording material of the present invention include paper, high grade paper, coated paper and other types of paper; films and resins such as polyester, polyethylene, polypropylene, cellulose acetate, cellulose ester, polyvinyl acetal, polystyrene, polycarbonate, polyethylene terephthalate, or polyimide; and synthetic paper or the like comprising paper and resin.
• films are preferred because they have excellent surface smoothness, strength, and the like, and because they are thin, with a thickness of not more than 0.05 mm and they therefore have a relatively small volume area when rolled. Forming a reflection layer by aluminum deposition or the like on at least one side of the film is effective for improving the photosensitivity of the photosensitive recording material.
• a hydrophilic binder is mixed in the microcapsule dispersed liquid to form a photosensitive layer by applying the microcapsules on the aforementioned recording medium.
• Natural substances such as gelatin, cellulose, starch, and gum arabic, or synthetic polymers such as polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, polymethacrylic acid, polyacrylamide, polyvinyl imidazole, and polystyrenesulfonic acid may be used as the hydrophilic binder.
• a photosensitive recording material using microcapsules containing a phosphine compound with the following composition and a photosensitive recording material using microcapsules containing no phosphine compound were applied to the surface of polyester sheets.
• the materials were exposed and hardened using a spectral sensitivity meter, and were then overlaid with image-receiving paper and pressurized.
• the hardening energy was measured based on the extent of hardness at the maximum image hardness wavelength, the radiating energy from the light source at that wavelength, and the exposure time, and the obtained value was considered an index of hardness.
• R 1 , R 2 , and R 3 are all -SR 4 , and R 4 is a C 12 straight-chain alkyl group.
• R 1 , R 2 , and R 3 are all C 6 aryl groups.
• R 1 , R 2 , and R 3 are all -OR 4 , and R 4 is a C 6 aryl group.
• the photosensitive recording materials in which the photopolymerizable unsaturated group-containing compound contained a phosphine compound can thus be said to be more sensitive to light and to have good hardening properties.
• the photosensitive recording material of the present invention allows the microcapsules to be sufficiently hardened with low energy, and clear images to be formed with good tone and no smearing.
• the photosensitive recording material of the present invention in which the photopolymerizable unsaturated group-containing compound is a polymerizable compound containing at least one ethylenic unsaturated double bond, allows the microcapsules to be sufficiently hardened rapidly, and clear images to be formed with good tone and no smearing.
• the photosensitive recording material of the present invention in which the phosphine compound is present in an amount of from about 0.01 to 20 wt%, allows the microcapsules to be sufficiently hardened in a rapid manner with low energy, and clear images to be formed with good tone and no smearing.

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• 1997
  • 1997-05-21 JP JP9130813A patent/JPH10319584A/ja active Pending
• 1998
  • 1998-05-15 US US09/079,366 patent/US6117609A/en not_active Expired - Lifetime
  • 1998-05-20 EP EP98304014A patent/EP0884650A1/en not_active Withdrawn

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